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Патент USA US3021243

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United States
Patented Feb. 13‘, 1962
——R— is not critical provided it is inert to reaction with
amines, it may be any member of the class consisting of
John Edward Pretka, Wilmington, Del., assignor to E. I.
du Pont de Nemours and Company, Wilmington, Del.,
0 H
H 0
and —A- wherein -A-- is a member of the class
consisting of divalent aliphatic, alicyclic, aromatic and
heterocyclic radicals. Preferably —A-— is hydrocarbon.
a corporation of Delaware
No Drawing. Filed Nov. 17, 1958, Ser. No. 774,138
13 Claims. (Cl. 117-1383)
A particularly desirable class of polyamines are those of
the formula:
This invention relates to new compositions of matter.
More particularly it is concerned with a synthetic, hydro
phobic sphaped structure bearing a novel ?nish to mini
mize the accumulation of charges of static electricity dur
ing ?nishing operations and normal use.
wherein—X» is a member of the class consisting of
One common disadvantage of synthetic, hydrophobic
shaped structures such ‘as foams, ?bers, ?laments, yarns,
staple, fabric, pellicles and the like, is that they tend to
develop static electrical charges. This feature is objec
tionable during the manufacture of textiles and in the 20
?nished garment. During manufacturing, static charge
wherein -—R' is a member of the class consisting of
from the ?bers or fabric interferes with convenient
hydrogen, lower alkyl (i.e., an alkyl radical containing
handling during spinning, reeling, weaving, and the like
less than about 8 carbon atoms in its longest chain) and
operations. Finished textiles containing such structures
amino lower alkyl and -Y-— is divalent aliphatic which
fail to drape like cotton or wool due to their static charge 25 while it may contain aza linkages is otherwise hydrocar
and have a tendency to cling uncomfortably to the
bon, q being a number from about 6 to about 40. The
wearer. Furthermore such textiles tend to collect dust
preparation of these polyamines is discussed in detail in
and lint. In addition, the electric discharge itself is
Belgian Patents 554,506, granted January 25, 1957, and
bothersome. Most known antistatic agents usefulin the
560,446, granted September 14, 1957. In general, the
textile arts lack durability and some impart to textiles
polyethylene glycol dihalide (e.g. chloride, bromide or
undesirable properties such as unpleasant hand and dis
iodide) analogue is condensed (with release of hydrogen
coloration upon application or with continued fabric use.
halide) with an amine, the nitrogen of which contains
Furthermore, some known antistatic agents are operable
at least two active hydrogen. Typical of such amines are
only within a narrow pH range and thus lack compati
ethylamine, propylamine, butylamine, amyl-_
bility with many other common yarn-treating agents 35 amine, hexylamine, dodecylamine, alylamine, mono
which are not stable in that pH range, making it necessary
ethanolamine, 3-isopropyl-n-propylamine, 3-methoxy-n
propylamine, diethylenetriamine, bis(3-aminopropyl)
to apply the agent in a treatment step distinct from that
employed for other purposes.
It is an object of the present invention to provide a
composition which will impart durable antistatic protec
.tion to a synthetic, hydrophobic shaped structure without
causing objectionable changes in other properties.
It is another object to provide a water-soluble anti
static composition which is compatible with pH sensi
tive yarn-?nishing ingredients.
A further object is to provide a treated synthetic, hy
drophobic shaped structure which minimizes or elimi
nates build-up of electrostatic charge and otherwise pos
‘amine, bis(2-aminopropyl)amine, hexamethylene dia
mine, triethylene tetramine, tetraethylene pentamine and
the like.
Such materials are available on the open
market, typical products corresponding in general to Ex
ample 10 of Belgian Patent 560,446 and Example 1 of
Belgian Patent 554,506. Assignee of the Belgian patent,
the Onyx Oil and Chemical Company of 115 Morris
Street, Jersey City, New Jersey, markets such products
under the trademarks Aston 108 and Aston LT.
By “epoxide curing” is meant that the polyamine de?ned
above is reacted, after application of the reactants to the
sesses substantially the same properties as the same struc
50 said shaped structure, with a polyepoxide. Such mate
ture before treatment.
rials can be prepared "by condensing epichlorohydrin with
Another object is to provide a process for imparting
a polyol. A typical example is the condensation product
durable antistatic properties to a synthetic, hydrophobic
(with elimination of HCl) of glycerine and epichloro
shaped structure.
hydrin. Preparation of these products is described in de
These and other objects will become apparent in the 55 tail in British Patent 780,288, dated July 31, 1957. Such
course of the following speci?cation and claims.
a material with a molecular weight of between about 280
In accordance with the present invention a synthetic,
to 360 is available on the open market under the trade
hydrophobic shaped structure which minimizes accumu
mark “Eponite 100” (viscosity 90-150 cp. at 25° C.; 10.2
lation of charges of static electricity is provided by epox
lbs./ gal.) by the Shell Chemical Corp. of 500 Fifth Ave
ide curing at a pH below 7.0 in the presence of an epox 60 nue, New York, N.Y. Other similar commercial prod
ide curing catalyst a synthetic hydrophobic shaped struc
ucts from the same source include the “Epon”- resins which
ture bearing a polyamine of the formula:
are diepoxide condensation products of epichlorohydrin
H [-X-CH2CH2-—( OCHZCHZ) m_"O-—R-——O
—(CH2CH2O)n-CH'2CH2],,—X--H (I)
wherein -R— is a divalent radical, —X— is a membei 65
and dimethyl, di-para hydroxyphenyl methane and the
poly(allyl glycidyl ethers). A typical siloxane is l,3~bis
[-3-(2,3-epoxy propoxy) propyl] tetramethyldisiloxane sold
of the class consisting of amino nitrogen and divalent
under the trade mark “Syl-Kern 90” by Dow Corning
radical terminating in amino nitrogen, m and n are small
whole numbers from about 3 to about 40 and p is an
integer no greater than about 10. Since the nature of
accomplished by heating the shaped structure to which an
Corp., Midland, Michigan. Reaction of the polyamine
(I) or (II) with the polyepoxide'may be conveniently
acidic mixture of the amine and polyepoxide has been
water. 62 parts of “Eponite 100” as identi?ed above is
then added and the mixture is dispersed using a Waring
Blender. While mixing in the Waring Blender, 4 parts
In the examples which follow, unless otherwise stated,
the “washed fabrics” are washed in a Kenmore portable
of zinc ?uoroborate catalyst as a 40% aqueous solution
washer at 140° F. using 0.125% “Tide” detergent in the 5 is
added. A slightly turbid solution is formed.
presence of a small amount of trisodium hexametaphos
swatch of tropical plain weave fabric woven from
phate, then thoroughly rinsed and dried. The dry clean
a polyethylene terephthalate yarn is dipped into the
ing operation employed involves a 25-minute tumble at
emulsion prepared as described above and squeezed be
room temperature using a solution of the following:
tween the rollers of a hand wringer. The fabric is then
10 cured for 5 minutes in an oven at 160° C. and there
30 parts by volume perchloroethylene
2.1 parts by volume dry cleaning soap (sold by R. R.
after scoured for 15 minutes at 140° F. The fabric is
observed to have gained 3.2% by weight of antistatic
Street 8; Co., Inc., 569 W. Monroe Street, Chicago,
?nish based on the original Weight of the fabric. The
treated fabric has a log R of 10.3 compared with an
, Illinois, under the trademark “Streets 886”)
0.2 part by volume water
After tumbling, the fabric is centrifuged for 6 minutes,
15 original log R of 14.2.
of fresh, uncharged solvent, then centrifuged again for
5 minutes, dried for 2 minutes at from 60—70‘’ C. and
steam pressed. The bleaching procedure, representative
of prevailing commercial practice, consists of immersing
fabric in 100 times its weight of bleaching bath containing:
employed using the technique described above. In this
20 case 80 parts of the zinc ?uoroborate catalyst is em
ployed. The product has a log R of 11.0 before the
standard bleaching and a log R of 11.5 after the bleach
Sodium chlorite _____________________________ __
_ _ _ __
_ _ _ _ __
After the standard bleaching the
sample is observed to have a log R of 12.9.
A 21% by weight ?nish based on the Weight of the
fabric is attained when 1240 parts of “Eponite 100” is
tumbled for an additional 5 minutes with an equal amount
Example 1 is modi?ed by employing as the polyamine
Nitric acid __________________________________ __ .11
component the reaction product of the dichloride of poly
Sodium nitrate ______________________________ __ .5
ethylene glycol having a molecular weight of 600 with
_____ 99
methylamine (“Aston 108” as identi?ed above). The
heating to boiling, maintaining at boiling for 1 hour, and 30 percent by weight of ?nish picked up by the fabric sam
subsequently rinsing the fabric in warm water. The
ples as Well as log Rs before and after standard bleach
bleaching operation is then completed by a scour, i.e.,
ing when using 62 parts of the diepoxide (A) and when
boiling the fabric for 30 minutes in 100 times it weight
using 1240 parts of the diepoxide (B) are shown in Ta
of a detergent mixture consisting of:
ble 1.
Table 1
Green soap ___________________________________ _ .1
Sodium lauryl sulfate
Trisodium phosphate
followed by fabric rinsing, dryn'ng, and steam pressing.
by Wt.
Durability of antistatic treatments to bleaching, wash 40
ing, and dry cleaning is determined by measurement of
Log R
A _______________________________ _ _
2. 8
B _______________________________ __
21. 0
surface resistances of the fabrics. These measurements
are made under controlled conditions of 25% relative
humidity and a temperature of 70° 1F. Current ?owing
Sample (B) is found to be waxy and stiff.
across, the fabric is measured accurately with a Beckman, 45
l0. 0
10. 6
10. 7
11. 7
Model V Micro-microammeter, and the surface resist
A Waring Blender is employed to mix 500 parts of
anee is then calculated from this and the known applied
“Aston 108” as a 20% solids solution in water, 100 parts
voltage. For convenience, these values are reported as
logarithms of surface resistance. In general, the lower
of a 10% aqueous solution of hydrochloric acid, 62 parts
the surface resistance, the lower is the tendency of the 50 of “Eponite 100” and 4 parts of zinc ?uoroborate catalyst
as a 40% aqueous solution. The pH of the resulting
fabric to develop a static charge. Surface re?ectance
mixture is 3.5. The mixture is then stirred into 4340
of undyed fabrics is used as a measure of whiteness.
parts of water. The ?nish is padded upon four fabric
Measurements are made using a Photovolt Model 610
swatches identi?ed in Table II.
re?ectometer. By using green, amber, and blue ?lters,
grayness and yellowness can be estimated.
bL=mlBl ( yellowness factor)
Table II
0 ________ . .
D ________ __
Tropical plain weave from polyethyleneterephthala to yarn.
Twill fabric woven from a yarn produced from a polymer of
B=,re?ectance with blue ?lter
G=re?ectance with green ?lter
The following examples are cited to illustrate the
invention. They are not intended to limit it in any way.
Unless otherwise noted, “parts” as expressed in the ex 65
acrylonitrile (“Orlon,” a trademarked product produced
11)); E. I. du Point de Nemours and Co. of Wilmington,
E ________ __ Tricot fabric knitted with a polyhexamethylene-adipamide
F ________ _.
Ta?e ta fabric woven from a polyhexamethylene-adiparnide
amples indicates parts by weight.
The ?nish is applied using a laboratory padder set at‘
50 lbs. per square inch providing t-wo dips and two nips.
100 parts of the polyamine formed by condensation
of diethylene triamine with the dichloride of polyethyl 70 After padding all fabric samples are dried overnight at
room temperature and thereafter cured for 6 minutes at
ene glycol having a molecular weight of 600 (“Aston
150° C. The initial log R of the samples, the percent
L ” as identi?ed above) as a 20% solids solution in
by weight of antistatic agent deposited based on the
water is stirred into 5000 parts of water. The pH of
weight of the fabric and the log R observations before
the resulting solution is adjusted to 3.2 by addition
after washing, bleaching and dry cleaning are shown
of 70 parts of a 10% solution of hydrochloric acid in 75 in Table
Table V
Table III
Finishing Soln.
Compn. (per 1000
Log R Treated
Log R
treated) (Percent
Log R
cc. H2O
After a Hrs.
1 Dry
Bleach Clean
(parts) wash washes washes
5 dry
10 dry
14. 2
>16. 3
>16. 3
14. 5
14. 7 ______ __
2. 5
6. 2
10. 9
l0. 7
13.9 ______________ 13.8 ______________ _
12. 3
12. 9
12. 3
14.6 ______________ __
14. 4
For comparative purposes swatches of sample fabrics
______________ __
14. 3
14. 6
C, D and E above are padded with a solution containing 15
A cationic blue tint when added to the compositions em
106 parts of water, 175 parts of an aqueous solution con
ployed in treating samples H, I and J results in reduction
taining 35 parts “Aston 108” and 17 parts of a 90%
of the color of the samples to less than that of the con
aqueous solution of the diiodide of polyethylene glycol
trol. In a similar manner optical whiteners and silicone
having a molecular weight of 600. The pH is adjusted
water proo?ng agents and other commonly used textile
with sodium hydroxide to 11.1. After drying at 212°
treating agents may be simultaneously applied with the
F. fabrics are cured for about 3 minutes at 300° F. and
antistatic agents of the present invention to perform their
thereafter scoured. The amount of ?nish pickup and
conventional roles.
the log R before and after and combination of one bleach
and one scour are shown in Table IV. Comparative
?gures for similar samples treated in accordance with 25
‘Examples 1 and 2 are modi?ed by employing as the
the present invention are included in the table. The
curing agent 62 parts of “Syl-Kem 90” as identi?ed above.
samples treated with the ?nish cross-linked ‘with the “di
The log R of the samples M and N respectively before
iodide” are labeled C1, D1 and E. In addition the table
scouring, after scouring and after 5 hours wash are re
shows a comparative ?gure of yellowness factor relative
to samples C and C1, D and D1. These compare to the 30 ported in Table VI.
Table VI
yellowness factor of the untreated controls of 2.02 and
5.8 respectively.
Log R
Table IV
Log R
1 Bleach,
5 hrs.
M _________________________ __
N __________________________ ._
Factor '
‘Solutions are made by adding 10 parts of the polyamine
2. 9
10. 9
12. 5
12. 8
A polyepoxide resin is prepared by mixing 15 parts of
sodium styrene sulfonate, 80 parts of diionized water,
0.15 part of glyceryl monooleate, .08 part of alkyl phen
45 oxy polyoxyethanol and 1.67 parts of glycidyl meth
acryate in a Waring Blendor to form an emulsion. The
emulsion is added to a 200 ml. 3-necked ?ask which is
then ?ushed with nitrogen.
of Example 2 as a 20% solids solution in water to 1000
.06 part of a,u-azobisiso
butyryl nitrile is then added and the reaction mass is
parts of water containing 2.5, 6.2 and 12.3 parts respec
tively, of “Epon” Resin 562, a condensation product of 50 lheated for 3 hours at 70° C. A thick semi-transparent
emulsion is formed.
epichlorhydrin and glycerine containing 2 epoxy groups
0.5 part of the polyamine, “Aston 108,” is mixed with
per molecule. To serve as control solutions, “Epon”
0.5 part of the polyepoxide resin prepared as identi?ed
Resin 562 is omitted from one solution of polyethylene
above to give an aqueous emulsion having 1% solids and
glycol amine, and similarly, a 1% solution of “Epon”
Resin 562 is prepared, omitting the polyamine. All solu 55 the mixture is applied to staple ?ber formed from a poly
mer of acrylonitrile (i.e. “Orlon” as identi?ed above).
tions are acidi?ed to pH 2.5 with HCl, including a pure
The product is observed to have a by, of 4.4. The log R
water control containing no other ingredients. Samples
values after 1, 5 and 10 washings (as described in Exam
‘of a tow of continuous ?laments formed from a polymer
ple 4) are listed below: '
of acryolnitrile (i.e. “Orlon” as identi?ed above) are
dipped into the test solutions at room temperature, wrung 60
out to a solution pick-up of 100% and cured in a drying
oven at 270° F. for ten minutes. The cured tow is con
verted into staple pads suitable for washing and testing
for antistatic properties.
In this example in determining the durability of the 65
antistatic properties, washing tests are carried out with
0.1% aqueous “Tide” using a 15-minute wash cycle at 60°
C. followed by two 5 minute rinses at 60° C.
To determine the durability of the antistatic properties
lwashing _________________________________ __ 10.7
5 washings ________________________________ __ 12.1
10 washings _______________________________ __ 13.4
The technique of Example 4 is followed in preparing
three antistatic ?nish reactants (M, N and 0) containing
the polyamine and polyepoxide resin in a 1:1 weight ratio.
Aston 108 is employed as the polyamine in each appli
to dry cleaning, quarter-pound staple samples, Wrapped 70 cation. The emulsions are applied to a fabric woven
in cheese cloth, are rolled for one-half hour in 13 pounds
of Stoddard solvent containing 0.75% of dry cleaning
soap (Streets 886 detergent). This is followed by two
_ 15-minute rinses with pure Stoddard solvent, centrifuging
after each rinse, and air drying.
from a polymer of acrylonitrile (i.e. “Orlon” as identi?ed
above) having an initial b;, of 3.0. The identity of the
polyepoxide curing agent employed in each ‘example is
identi?ed in Table VII. The color and log R of each
75 sample after curing is reported in Table VIII.
Table VII
as the minor constituent in forming useful copolymers
with acrylonitn'le are listed in United States Patents Nos.
Polyepoxide Curing Agent
2,837,501; 2,486,241 and 2,436,926.
Eponite 100.
Epon 815.1
Poly allyl glycidyl other.
The polyesters from which such structures may be
‘devised include polyethylene terephthalate, polyethylene
terephthalate copolyesters prepared using polyethylene
glycols such as polyethylene glycols having molecular
1 A diepoxide condensation product of epichlorohydrin and dimethyl
Weights of 150 to about 6,000, or polyethers such as the
di-para hydroxyphenyl methane.
dicarboxymethyl acid of polytetramethylene oxide or the
esters polytetramethylene oxide, polydioxalane, or poly
137 s 15
esters prepared using other acids such as bibenzoic, iso
phthalic or ethylene-bis-p-oxybenzoic acids. Such mate
rials are described in United States Patent No. 2,465,319.
Application of the antistatic ?nish of the present inven
tion may be made to any form of the shaped structure in
Table VIII
1 Bleach 5 Washes
M ___________________________ __
4. s
N_ _ _ _ . _ _ _ _ _ _ _ .
3. 9
l3. 6
. _ _ i . _ _ __
0 ______________________________________________ _-
13. 9
l 13. 3
l3. 6
1 Log R after one wash is 12.6.
cluding foams, fabric, yarn, tow, staple, ?lms, plastic
sheeting and the like.
As described previously, the shaped structure is treated
With an emulsion of a mixture of a polyepoxide and a
20 compound of Formula I. Generally the emulsion is pre
pared by dispersing the polyamine and the polyepoxide in
A mixture of 50 parts of “Aston 108” (20% active in
water at room temperature with vigorous stirring. The
gredients), 10 parts “Eponite 100” and 940 parts water
is made up and adjusted to pH 3.5. A tow formed from
concentration of reactants in the emulsion may vary
widely. A concentration as high as 20% may be used.
a polymer of acrylonitrile (i.e. “Orion” as identi?ed
above) is treated to provide a 100% by weight wet pickup 25 However, more dilute emulsions containing from about 1
to about 5% of reactants are generally preferred. Any
of this solution, then cut into staple and dried at 270° F.
such ?nishing suspension having a concentration suitable
for ten minutes. 20 parts of this treated staple is then
to provide from about a 0.3% to about a 5% solids pickup
blended with 80 parts untreated staple and the blend is
based on the dry material is satisfactory. The reaction
spun into yarn ‘and woven into a twill fabric. Samples of
the fabric are washed, tested, ‘bleached, disperse dyed and 302 product can be applied to the structure by conventional
methods such as dipping, padding, brushing, spraying, and
basic dyed. All exhibit static protection after 10 washes
as shown in Table IX.
the like. After removal of excess liquid, by wringing in
the case of a textile, it is usually convenient to dry and
Table IX
F’ cure the structure in one operation.
In forming the mixture of reactants the proportion of
Log R
components may vary over a wide range. Preferably the
greige fabric ______________ ._
cotton wool
ratio of polyamine:polyepoxide is maintained within the
limits of 10:3 to 10:7. Higher ratios of polyepoxide
After 10
4. 9
0. 7
12. 5
After 10 > After 5
12. 7
cleanings 4Q such as 1:'l may be used however, as illustrated in the
examples. Larger amounts of the polyepoxide may be
employed but generally result in a harsher hand.
While, as illustrated above, the reactants may be applied
to the shaped structure without the presence of catalysts,
13. 7
it is preferred to include a minor amount of an epoxide
curing catalyst. Such materials not only hasten the cur-_
ing operation or permit curing at lower temperature, but
By the expression “. . . synthetic,v hydrophobic shaped
also increase adherence of the antistatic agent to the struc
ture. Such materials are well known in the art, as de
structure . . .” is meant a structure such‘ as a foam, ?ber,
?lament, yarn, staple, fabric, pellicle and the like, pro‘
scribed, for instance in United States Patent No. 2,752,269.
duced from a synthetic polymeric material, having a 50 Although the reacted mixture may be either acidic or
moisture regain of no greater than 5%, such as a poly
alkaline, alkaline conditions usually cause yellowing.
Optimum conditions of curing will depend upon the
amide, a polymer produced from acrylonitrile, a polyester,
or the like. Suitable polyamides are those produced from
identity of the reactants, the identity of the textile and
a linear polymer containing recurring units of the for
whether or not a catalyst is included. Room tempera
55 ture is adequate for forming the cured antistatic ?nish
when a catalyst is used. Generally, however, a tempera
ture of at least about 240° F. is preferred to accomplish
e?icient drying of the textile. Usually temperature ad
iustment is made to permit curing and drying in a 3
wherein Z is a member of the class consisting of a di
valent hydrocarbon radical and a divalent radical of the 60 minute interval. A temperature of about 212° F. to
250° F. is recommended for most textile materials. For
operation in the absence of a catalyst at curing cycle of
about 10 minutes at 270° F. is adequate.
While applicant does not wish to be bound by any
wherein G and G’ are divalent hydrocarbon radicals.
Typical polyamides and processes for their production are
described in United States Patents Nos. 2,071,250; 2,071,
253 and 2,130,948.
particular theory of mechanism, it is believed that the
curing operation is accomplished by reaction of the epox
ide with free hydrogen on the nitrogen of the polyamine.
Thus it has been observed that fabrics treated with poly
amines containing high proportions of active hydrogen
The term “polymer of acrylonitrile” is intended to in 70 (Aston LT) are stiffened to a greater extent upon curing
than those where the polyamine has less free hydrogen
clude any polymer of acrylonitrile including polyacrylo
nitrile (i.e., the homopolymcr) wherein the acrylonitrile
component constitutes about 85% or more of the polymer
(Aston 108).
Many modi?cations of the above will ‘be obvious to
molecule calculated as CH2=CH——CN. Many of the
those skilled in the art without a departure from the in
ethylenically unsaturated compounds which are suitable 75 ventive concept.
and thereafter reacting the said polyepoxide and the said
What is claimed is:
1. A process of minimizing the accumulation of charge
of static electricity upon a synthetic, hydrophobic shaped
structure which comprises applying to the said structure
polyamine together.
4. The process of claim 3 wherein the shaped structure
is a textile.
5. The process of claim 1 wherein the said polyepoxide
at a pH below 7.0 and in the presence of an epoxide cur
curing catalyst is zinc ?uoroborate..
ing catalyst, a mixture of a polyepoxide and a polyamine
of the formula:
6‘. The process of claim 3 wherein
wherein —R— is an organic divalent radical, -—X—— is
a member of the class consisting of amino nitrogen and
divalent radical terminating in amino nitrogen, m and n
are small whole numbers from about 3 to about 40 and p
is an integer no greater than about 10 and thereafter re 15
7. The process of claim 3 wherein
acting the said polyepoxide and the said polyamine to
2. The process of claim 1 wherein the shaped structure
is divalent ethylene triamine.
8. The process of claim 2 wherein the said textile is
is a textile.
3. A process of minimizing the accumulation of charge
of static electricity upon a synthetic, hydrophobic shaped
a fabric.
9. The process of claim 2 wherein the said textile is
structure which comprises applying to the said structure
a ?lament.
at a pH below 7.0 and in the presence of an epoxide cur
10. The process of claim 2 wherein the yarn of the
ing catalyst, a mixture of a polyepoxide and polyamine of
said textile is produced from a polymer of acrylonitrile.
the formula:
11. The process of claim 2 wherein the yarn of the
H [—X—CH2CH2—( OCHZCHZ) o—OCH2CHz] p—-X-—H
wherein —X- is a member of the class consisting of
said textile is a polyamide .
12. The process of claim 2 wherein the yarn of the said
textile is a polyester.
13. The process of claim 1 wherein at least about 0.3%
solids based on the dry material of the epoxide cured
polyamine is applied to the said structure.
References Cited in the ?le of this patent
wherein —R’ is a member of the class consisting of hydro
gen, lower alkyl and amino lower alkyl, --Y—— is a mem
Schroeder ____________ _- June 4, 1957
Belgium ____________ __ Jan. 27, 1957
ber of the class consisting of divalent aliphatic hydrocar
bon and aza containing alkylene, q is a number from about 40
6 to about 40 and p is an integer no greater than about 10
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